Formaldehyde → HCID 10339487, compound

Participants

Reaction Steps

A 28 mL Pyrex-Plus tube containing the product of Example 1, Step 9 (30 mg, 0.086 mmol) was charged with methanol (1.0 mL), then acetic acid (33 □L), then formaldehyde (28 mg of a 37% aqueous solution, 0.34 mmol), then NaBH3CN (431 □L of a 1.0M solution in THF, 0.431 mmol), and stirred at room temperature for 12 hours. A separate 28 mL Pyrex-Plus tube containing the product of Example 1, Step 9 (70 mg, 0.20 mmol) was charged with methanol (2.0 mL), then acetic acid (67 □L), then formaldehyde (65 mg of a 37% aqueous solution, 0.80 mmol), then NaBH3CN (1.00 mL of a 1.0M solution in THF, 1.00 mmol), and stirred at room temperature for 2 hours. Both reaction mixtures were then combined, along with 50 mgs of crude product prepared previously then concentrated under reduced pressure, then dissolved in a minimum volume of methylene chloride, then injected directly onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure, yielding 110 mg of dimethylamine 25. This sample was dissolved in 4 mL methanol and purified on an HPLC column, from 4×1.0 mL injections, using a gradient that started at 40% methanol and 60% water and ended at 100% methanol. Fractions containing desired product were pooled and concentrated under reduced pressure. Quantity isolated of 25: 68 mg. 1H NMR (500 MHz, CDCl3) δ 2.33 (s, 6H), 2.64 (t, J=7.8 Hz, 2H), 2.89 (t, J=7.8 Hz, 2H), 5.11 (bs, 2H), 6.52 (d, J=5.5 Hz, 1H), 6.83 (dd, J=7.0, 2.0 Hz, 1H), 7.14 (m, 2H), 7.52 (dd, J=1.8, 0.5 Hz, 1H), 7.65 (m, 2H), 8.12 (d, J=5.5 Hz, 1H), 9.44 (dd, J=7.5, 0.5 Hz, 1H). MS (ESI+) 377.4.

Provenance & Evidence